Dread Pirate Roberts: The lord of the Silk Road confounds expectations
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by C.J. McKinney


The Silk Road is dead, but the story of the Dread Pirate Roberts lives on.

The name comes from a tongue-in-cheek cult classic movie called The Princess Bride. But to the users of the Internet drug marketplace Silk Road and law enforcement authorities the world over, it’s the online moniker of Silk Road’s mysterious architect – a man both reviled as a drug trafficker and contract killer, and revered as a champion of personal liberties and the freedom of the Internet.

Silk Road was shut down by the FBI and international authorities in 2013 for its role as an online meeting place for unbridled trafficking in illegal substances – and activities – of all kinds, no questions asked. The secret to the site’s success was its embrace of cutting edge technology. And the linchpins of that success were the digital currency Bitcoin and the cloaking network Tor.

Bitcoin appeared on the international monetary scene a few years ago, the brainchild of a largely anonymous consortium of computer experts who created it as a completely digital form of exchange that didn’t depend on the traditional banking structure. Because the Bitcoin is a completely digital entity, it can be exchanged for anything as long as the parties involved agree to the transaction.  It’s completely stateless and almost totally anonymous, so its users can’t be traced through any of the usual avenues for tracking financial dealings in the world of conventional banking.

That made Bitcoin the darling of  civil libertarians everywhere, who saw it as a step toward the democratization of currency. Those same reasons made it the coin of choice for  Silk Road.  When the site was shut down, the FBI and other authorities confiscated over  $1 million in Bitcoin, which is now being auctioned off by US marshals in batches to unnamed bidders.

Access to Bitcoin on Silk Road site was supported by Tor, a network whose sole purpose is to hide IP addresses and wrap communications in layer upon layer of encryption.  To get access to the marketplace, all users had to do was to install Tor’s software, type in Silk Road’s address and start shopping. The site featured instant access to major Bitcoin exchanges such as Mt Gox and others, so users could conduct transactions virtually instantly.

Silk Road was nothing if not eclectic.  According to the New York Times, FBI files on the takedown reveal over 13,000 listings for various banned and controlled substances, plus sections for “services” like tutorials on hacking ATMs and “digital goods” such as false documents and stolen internet accounts.

Behind all this stands the cryptic figure of Dread Pirate Roberts, an individual whose online identity became famous among the denizens of the “Dark Web,” an Internet world of black marketers and shady dealers from all corners of the world. The Pirate himself was rarely heard and never seen, not even by the site’s small staff. But his writings appeared regularly on  Silk Road’s blog, where he even created a book club for the site’s community.  And it’s hose writings that reveal an agenda that goes far beyond the conducting of a profitable illegal business.

In his posts and messages to the Silk Road community, the Pirate spoke often of the need for personal privacy and the right to conduct business – any business – as one chooses, no questions asked.  He writes of the need for everyone to speak out in support of those freedoms and resist the incursions by authorities into individual lives.

By the end of 2013, the Pirate’s individual life was a good one indeed. In just two and a half years Silk Road was enjoying huge success and the Pirate was a multibillionaire.  But buzz about the site brought it onto the radar of DEA authorities, who sent task force members undercover on the site.  Investigations followed, and Silk Road was shut down and its assets confiscated.

But Dread Pirate Roberts remained elusive.  He became the target of multiple investigations and charges began to fly, ranging from drug trafficking to murder for hire. Eventually authorities arrested a young American named Ross Ulbricht as the mastermind behind Silk Road.

It’s not entirely clear how the FBI and Homeland Security managed to identify Ulbricht as Silk Road’s dread drug lord.  Details involved postings to a Bitcoin forum and suspect packages sent to his address, along with murky links to arrangements for killing the suspected mole. Those allegations and others including drug trafficking and identity theft will be debated in court in January 2015, when defense attorneys are prepared to challenge the government’s claim that Ross Ulbricht is in fact the Dread Pirate.

At the time of his arrest, Ross Ulbricht was just 29 years old, a young man who by the accounts of family and friends is shy and sensitive, with hopes of making a lasting impact on humanity.  But he also believed passionately in “eliminating coercion,” and helping people live their lives free of the imposition of force from sources of authority.

It’s words like those, rather than the convoluted legal trail that led to Ulbricht’s arrest, that create the strongest link between him and the Dread Pirate, whose writings on Silk Road made the same passionate call for people to throw off their chains, embrace the freedoms created by technology, and launch a revolution for personal independence.

Whether or not Ross Ulbricht of Austin, Texas is really the Pirate, that contradictory figure lurking in the shadows of the Dark Web may be a bit of both, headed for a place in that long line of legendary outlaws who challenged oppressors and championed freedom.


Image: Flick/the frog’s eyebrow





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I\'m a freelance writer. indie publisher and digital designer specializing in ebook production and website content.

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